Falls remain the leading cause of injuries and fatalities in residential construction. Because of job-specific work conditions and environmental constraints, the various construction trades (e.g., roofing, siding, or framing) employ different safety standards and fall-protection training practices. The purpose of this study, therefore, was to explore the specific training needs and training preferences of small roofing subcontractors. A total of 20 roofing subcontractors participated in this study. A mixed methods approach, incorporating a survey and semi-structured interviews, was utilized. Results from this study revealed that an individual's job title (i.e., his or her role on the jobsite) and the employer's existing training methods were accurate predictors of the employee's preferred training methods. This study also suggests the need for improved fall hazard awareness among roofing workers via training. Context-relevant methods and workers' preferred physical forms in receiving training were identified and found to be most effective for safety training and learning in the workplace.